Anthraquinone dye and process of making same.



UNITED STATES PATENT FFICE.

MAX I-I. ISLER, OF MANNHEIM, GERMANY, ASSIGNOR TO BADISOHE ANILIN do SODA FABRIK, OF LUDWIGSHAFEN, GERMANY, A CORPORATION OF GERMANY.

ANTHRAQUINONE DYE AND PROCESS OF MAKING SAME.

SPECIFICATION forming part Of Letters Patent 'NO. 690,292, dated Deceiilber 31 1901.

Application filed October 8, 1901- Serial No. 78,000. (No specimens.)

To all whmn it Tmty concern:

Be it known that I, MAX HEINRICH IsLER, chemist, a citizen of the Swiss Republic, residing at Mannheim, in the Grand Duchy of Baden, Germany, have invented new and useful Improvements in new Anthraquinone Goloring-Matters and Processes of Producing the Same, of which the following is a specification.

Upon treating mono-amido-beta-methyl- 1o anthraquinone with bromin brom-amido-methyl-anthraquinone is obtained. If this brominated body be treated with potassium nitrite in concentrated sulfuric acid on the water-bath, the amido group is replaced by a bydroxyl group. Similarly, also, an analogous chlorin derivative can be obtained. I have discovered that this brom or chlor hydroxymethyl-anthraquinone can readily be made to react with aromatic amins, whereby new col- 2o oringmatters are produced, which in the form of sulfo-acids dye WOOl violet shades of greater brightness than those obtained from any alizarin colors hitherto known.

The following examples will serve to further illustrate the nature of this invention and the manner in which the same may be carried into practical efiect; but the invention is not confined to these examples. The parts are by weight.

Example 1: Mix together ten (10) parts of brom-hydroxy-methyl-anthraquinone, ten (10) parts of sodium acetate, (free from water,) and one hundred (100) parts of para-toluidin. Heat the mixture so that it boils and 3 5 maintain the heat until no further formation of coloring-matter can be observed. Dilute the melt with three (3) times its weight of alcohol and allow it to cool. The new coloringmatter separates out in the crystalline form. Collect by filtering, and if it be desired to purify recrystallize from glacial acetic acid. The filtrate upon treatment with dilute hydrochloric acid yields a coloring-matter which upon sulfonation dyes wool, yielding greener and duller shades than the sulfo-acid of the main product.

In the foregoing example the sodium acetate prescribed need not be added; but it improves the yield of the coloring-matter. In-

stead of para-toluidin other aromatic amins can be employed, such as anilin, which yields a similar coloring-matter.

The brom-hyin hot water.

Pour the melt into water, precipitate by means of common salt or potassium chlorid, filter, wash with common salt solution, press, and dry. Instead ofsulfonating with monohydrate other concentrated acid or fuming acid, with or without the addition of horacic acid, can be used.

The following table shows some of the reactions and properties of certain coloringmatters obtained according to my invention:

Coloring-matter from bromhydroxy-methyl-anthraquinone and- Anilin. Toluidin.

(a) Unsulfonated.

Appearance of the coloring- Violet-brown Dark violet.

matter. Solution in concentrated sul Blue-green Blue-green.

furic acid. Solution in concentrated sul- Violet Blue.

furic acid and boracic acid. Solution in alcohol Red-violet Violet. Solution in anilin Blue violet Blue.

(12) Sulfonated.

Dyes uninordanted wool Red-violet Pure violet. Dyes chrome mordanted wool Duller violet Blue-green. Solution in water Violet Violet-blue. On addition of caustic soda Blue Blue. Solution in concentrated sul Red-violet.. Do.

furic acid.

The same upon addition of bo- Becomesconsid- B e c o m e s racic acid. erably redder. redder. Solution in alcohol Violet-red.. Blue-violet. Solution in anilln Very difficultly Blue.

soluble Solution in pyridin Do.

Violet-red W What I claim istic soda becoming blue, which dissolves in.

concentrated sulfuric acid the solution being red-violet to blue and becomingredder on the addition of boracic acid, whose alcoholic solution is violet, and which dyes unmordanted wool violet shades, substantially as described.

4. The new coloring-matter such as can be obtained by condensing brom-hydroxy methyl-anthraquinone with para-toluidin, which in the unsulfonated form dissolves in sulfuric acid with a blue-green color, this color'on the addition of boracic acid becoming blue, Whose solution in anilin is blue and in alcohol violet, which in the sulfonated form dissolves in Water yielding a violet-blue solution, this solution on the addition of caustic soda becoming blue, and in sulfuric acid with a blue color, this solution on the addition of boracic acid becoming redder, whose alcoholic solution is blue-violet and which dyes uumordanted Wool pure violet shades, substantially as described.

Iii testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.

MAX H. ISLER.

Vitnesses:

ERNEST F. EHRHARDT,

JACOB ADRIAN. 

